ผลิตภัณฑ์ธรรมชาติเพื่อสุขภาพและความงาม Natural Products for Health and Beauty

1. ผลิตภัณฑ์ธรรมชาติเพื่อสุขภาพและความงามผลิตภัณฑ์ธรรมชาติเพื่อสุขภาพและความงาม Natural Products for Health and Beauty รหัสวิชา 1162202 หน่วยกิต3(2-2-5) วิชาเอก (เลือก) อ. ดร. วรวัฒน์ พรหมเด่น สาขาวิชาวิทยาศาสตร์ทั่วไป คณะครุศาสตร์ มหาวิทยาลัยราชภัฏบุรีรัมย์

2. สารทุติยภูมิ (Secondary metabolites) สารอัลคาลอยด์ (Alkaloids) 2. กลุ่มสารฟีนอลิก (phenolic compounds) - Simple Phenols / Phenolic acids / Phonolic glycosides - Coumarins - Flavonoids - Tanins - Quinones กลุ่มสารเทอร์พีนอยด์ และ สเตียรอยด์ (Terpenoids and Steroids) - monoterpenes, sesquiterpenes, diterpenes, triterpene, tertraterpenes, volatile oils, resins and oleoresins กลัยโคไซด์อื่นๆ (other glycosides) - cyanogenic glycosides, glucosinolate compounds

3. เทอร์พีนอยด์ (Terpenoids) หรือ เทอร์พีน (Terpenes) บางครั้งอาจเรียกว่า isoprenoidsเป็นสารทุติยภูมิกลุ่มใหญ่ ที่พบมากที่สุดในธรรมชาติ สามารถพบได้ทั้งในพืชและในสัตว์ พบในฮอร์โมนของแมลง ในสัตว์ทะเลจำนวกฟองน้ำ เทอพีนอยด์ประกอบด้วยหน่วยย่อยเรียกว่า isoprene unit ซึ่งเป็นสารประกอบ ไฮโดรคาร์บอนที่มีสูตรเป็น CH2=C(CH3)CH=CH2

4. Plant terpenoids are used extensively for their aromatic qualities and play a role in traditional herbal remedies. Terpenoids contribute to the scent of eucalyptus, the flavors of cinnamon, cloves, and ginger, the yellow color in sunflowers, and the red color in tomatoes. cinnamon Eucalyptus essential oil Clove essential oil

5. Well-known terpenoids include citral, menthol, camphor. Geranial (E-isomer of citral) menthol Neral (Z-isomer of citral) camphor

6. Structure and classification • The terpenoids can be classified according to the number of isoprene units used: • Hemiterpenoids, 1 isoprene unit (5 carbons) • Monoterpenoids, 2 isoprene units (10C) • Sesquiterpenoids, 3 isoprene units (15C) • Diterpenoids, 4 isoprene units (20C) (e.g. ginkgolides) • Sesterterpenoids, 5 isoprene units (25C) • Triterpenoids, 6 isoprene units (30C) (e.g. sterols) • Tetraterpenoids, 8 isoprene units (40C) (e.g. carotenoids) • Polyterpenoid with a larger number of isoprene units

8. Hemiterpenes consist of a single isoprene unit. Isoprene itself is considered the only hemiterpene, but oxygen-containing derivatives such as prenol and isovaleric acid are hemiterpenoids. prenol isovaleric acid Prenol occurs naturally in citrus fruits, cranberry, bilberry, currants, grapes, raspberry, blackberry, tomato (3-Methylbutanoic acid) isovaleric acid is a major component of the cause of unpleasant foot odor, as it is produced by skin bacteria metabolizing leucine.

9. Monoterpenes consist of two isoprene units and have the molecular formula C10H16. Examples of monoterpenes and monoterpenoids include geraniol, terpineol (present in lilacs), limonene (present in citrus fruits), myrcene (present in hops), linalool (present in lavender) or pinene (present in pine trees) Terpineol Syringa vulgaris (lilacs) Geraniol Family: Oleaceae

10. Monoterpenes citrus fruits Family: Rutaceae limonene myrcene Hop flower Humuluslupulus Family: Cannabaceae

11. Monoterpenes Portuguese lavender linalool Lavandulalatifolia Family: Lamiaceae (+)-α-Pinene pine trees Family: Pinaceae

12. Sesquiterpenesconsist of three isoprene units and have the molecular formula C15H24. Examples of sesquiterpenes and sesquiterpenoids include humulene, farnesene, farnesol, gossypol, picrotoxin, santonin, artemisnin. • Chemical structure • Plant name / plant organ • Usefulness (The sesqui- prefix means one and a half.)

13. Diterpenes are composed of four isoprene units and have the molecular formula C20H32. They derive from geranylgeranyl pyrophosphate. Examples of diterpenes and diterpenoids are cafestol, kahweol, cembrene and taxadiene (precursor of taxol), stevioside, andrographolide and plaunotol. Diterpenes also form the basis for biologically important compounds such as retinol, retinal, and phytol. • Chemical structure • Plant name / plant organ • Usefulness

14. Sesterterpenes, terpenes having 25 carbons and five isoprene units, are rare relative to the other sizes. (The sester- prefix means half to three, i.e. two and a half.) An example of a sesterterpenoid is geranylfarnesol. • Chemical structure • Plant name / plant organ • Usefulness

15. Triterpenes consist of six isoprene units and have the molecular formula C30H48. The linear triterpenesqualene, the major constituent of shark liver oil, is derived from the reductive coupling of two molecules of farnesyl pyrophosphate. Squaleneis then processed biosynthetically to generate either lanosterol or cycloartenol, the structural precursors to all the steroids. • Chemical structure • Plant name / plant organ • Usefulness

16. Sesquarterpenes are composed of seven isoprene units and have the molecular formula C35H56. Sesquarterpenes are typically microbial in their origin. Examples of sesquarterpenoids areferrugicadioland tetraprenylcurcumene. • Chemical structure • Plant name / plant organ • Usefulness

17. Tetraterpenescontain eight isoprene units and have the molecular formula C40H64 . Examples of tetraterpenes are capsanthin and capsorubin extracted from the fruits of Capsicum annuumor Capsicum frutescens. Biologically important tetraterpenoids include the acyclic lycopene, the monocyclic gamma-carotene, and the bicyclic alpha- and beta-carotenes. • Chemical structure • Plant name / plant organ • Usefulness

18. Polyterpenesconsist of long chains of many isoprene units. Natural rubber consists of polyisoprene in which the double bonds are cis. Some plants produce a polyisoprene with trans double bonds, known as gutta-percha. • Chemical structure • Plant name / plant organ • Usefulness